


The Company Makes A Difference

by BeanieJedi33



Series: Life Lessons Learned [6]
Category: Supernatural
Genre: Cas is supportive, Castiel and Dean Winchester in Love, Chuck is a bad dad, College Student Dean Winchester, Date Night, Dean Winchester In Love, Dean and cas learn more about each other, Dean falls in love with Cas, Dean likes Rom Coms, Dean likes Shakespeare, Emotional Hurt/Comfort, Falling In Love, Fluff, John Winchester's A+ Parenting, Kissing, Light Angst, M/M, Making Out, Midnight Walk, Nerd Dean Winchester, Professor Castiel, Smart Dean Winchester, Sneaking Around, Student Dean Winchester, Supportive boyfriend Castiel, Tooth-Rotting Fluff, dinner date, theatre date
Language: English
Status: Completed
Published: 2018-09-07
Updated: 2018-09-07
Packaged: 2019-07-07 23:16:33
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,267
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15918243
Author URL: https://archiveofourown.org/users/BeanieJedi33/pseuds/BeanieJedi33
Summary: Dean has a study session on Friday night, that Anna invites him to, but Anna isn't up for just studying. Saturday night, Dean and Cas have a romantic date where they learn more about each other's past, go to the theatre to see a play, and have a midnight walk.





	The Company Makes A Difference

Dean threw on his black suit jacket, took one last look in the mirror to make sure his tie was straight, and headed out the door. He was so nervous for tonight’s date with Cas. For starters, he didn’t know much about theatre, but Cas really wanted to see a play. Dean didn’t want to look like an idiot, so he thought he could look up some information about the play, before he went, so he could impress Cas. However, Cas refused to tell him what the play was about, wanting to surprise Dean. The only thing Cas told him was he needed to wear a suit for both the dinner and the play. Dean was also nervous, because last night, during his group study session, Anna had invited him to study again at her place again tonight, and Dean had to come up with an awkward excuse. One another than he was going out with their professor for dinner, theatre, and a midnight walk. 

_Last Night (Friday)_

Dean finished his last class of the day and made his way back to his apartment. As soon as he stumbled into his apartment he threw his bag next to the couch and collapsed on it. 

_Thank God it was Friday_

Dean was lying down, all stretched out on the couch, when he felt his phone vibrate.

From Anna: _Hey, Dean. It’s Anna from mythology. A few of us are getting together around 7 tonight to study. It’s in my apartment. Wanna come?_

Dean really didn’t wanna go, but he agreed to be a part of the study group, and he didn’t want to look suspicious. He thought a few people had started to notice he went to Dr. Novak’s office hours every time he had them. Dean didn’t want people to think the reason was anything other than he was just a very serious student and wanted to ask extra questions, so he agreed to go to the study group.

To Anna: _Sure. I’ll be there around 7_

From Anna: _Great. Can’t wait_

Anna ended the text with a winkie-faced emoji.

Dean opened the text, but didn’t reply. He set his alarm for 6:45 and set his phone on the table beside the couch. It had a been a rough week. Midterms were starting up and homework was pilling up. Senior year was shaping up to be a rough year. At least he had Dr. Novak. That was Dean’s last thought before he fell asleep.

He woke up a few hours later to the sound of an obnoxious alarm going off. Dean turned off his alarm and got off the couch. He had 15 minutes before he had to be at his study group. He figured he should clean himself up a bit and not look like he’d just slept for a few hours. He headed to his room to put on a clean shirt and spray on cologne. 

_I wonder if they’re going to ask me about Dr. Novak, and all the times I’ve been in his office? Will they ask what we’ve talked about? Are they going to think I know more than them? Will they ask me questions if they don’t know the answer to something?_

Dean’s mind was racing when he heard his phone vibrate, jolting him out of his panic. Dean picked up the phone and saw it was Cas.

“Hey, Cas,” Dean answered.

“Hello, Dean,” Cas replied.

“What’s up?”

“Well, you seemed pretty stressed today in class, so I wanted to make sure you were okay. I know midterms are starting up and we have ours next week, so I just wanted to make sure you were okay, and if you need someone to talk to, you can always come to me,”

“Thanks, Cas. Yeah, with midterms starting up it’s been kinda crazy lately. I’m actually meeting with that study group I told you about in a few minutes,”

“That’s great, Dean,”

“Yeah. Just a little worried they’re going to ask me what I’ve been doing so much in your office and they may think I know more about mythology, because I’ve been in your office so much,”

“Dean, you do know more than them. I know we often talk when you’re in my office about other things, but you do always bring up something we talked about in class. You ask extra questions and we discuss the myths we talk about in class. Give yourself more credit, Dean. You spend extra time in my office, and yes, it’s partly because you’re my boyfriend, but you also know a lot about the material and we discuss it. You have very insightful interpretations and you know a lot more than you think you do, Dean,”

“Wow, Cas. I, uh, don’t really know what to say,” 

“Just go to your group, be your charming self, and impress them with all the things we’ve discussed,”

“Thanks, Cas,”

“You’re welcome,”

“I’ll see you tomorrow,”

“I can’t wait,”

“Me neither,” Dean hung up and was feeling confident after Cas’ talk. 

Dean grabbed his backpack and headed down the hall to Anna’s apartment. When he made it, he knocked on the door.

“Hey, Dean,” Anna answered.

“Hey, Anna,” Dean replied.

“Come on in. We were just about to start in a few minutes,” 

Anna led him over to the table where everyone was studying and sat down in her chair.

“Here, Dean, there’s an empty seat right next to me,” Anna said, tapping the spot next to her.

Dean thought she seemed a little too happy to have Dean sitting next to her for a study session, but he sat down there anyway since it was the only place to sit.

“So, we were just about to start studying and going over the different gods in Greek myths” Anna said, “Dean, why don’t you start?”

“Are you sure? I don’t wanna interrupt anything you guys were already doing,”

“Don’t be silly. We were waiting for you, so we haven’t started,”

“You could’ve started without me. You guys didn’t have to wait for me,” Dean said.

“That would’ve been rude, Dean. We wanted to make sure everyone was here before we started,” Another red-headed girl name Charlie said. Dean recognized her not only from this building, but she’d also been in a few of his math classes over the past few years. She was cool to hang out with, and made a great study partner.

“Yeah and besides, we wouldn’t have started without the genius of the group,” Anna said, gazing at Dean.

“I’m not a genius, guys,” Dean chuckled nervously.

“I think you are,” Anna said, “You always know the answers to the questions Dr. Novak asks, and you go to almost all his office hours. Clearly, you know a lot,”

“Well, I guess,” Dean said.

“Great, well, let’s get started. And remember, if you have any questions, make sure to ask Dean,” Anna said.

About two hours in, they’d covered half of the material that would be on their first exam. Dean knew all the answers to the questions everyone was asking him. Even questions on things they hadn’t covered in class, he knew the answer to, because he went to Cas’ office hours. 

_Maybe Cas was right after all. I do know this stuff, and a lot better than I thought I did_ Dean smiled to himself. 

“Okay, guys, it’s been a couple hours. Whose up for a study break and pizza?” Anna asked the group.

Everyone was up for that. Everyone agreed to contribute a few dollars for the pizza they ordered. About 20 minutes later the pizza arrived. They all took their places at the table, and of course, Anna sat next to Dean.

“So, Dean,” Jo started, “Why do you go to all of Dr. Novak’s office hours?”

“Yeah, you clearly know this stuff better than most of us, so why do you go, if you don’t need the help?” Anna chimed in, leaning in towards Dean.

“Well, you can never know too much. And no matter how much you know you can always know something more,” Dean said.

“Wow, Dean. That’s such a great way to think,” Anna said, rubbing her hand up and down Dean’s forearm.

“Yeah,” Dean blushed, not really knowing what else to say, so he awkwardly leaned away from Anna’s touch, by going for another slice of pizza.

“Am I the only one, or does anyone else think Dr. Novak is kind of cute?” Meg asked.

“Meg!” Charlie cried.

“What? I mean, it’s not like we all haven’t noticed. That voice of his, those bright blue eyes,” Meg started to day dream, “C’mon, don’t tell me I’m the only one who noticed that our professor is hot?”

“It’s true. I mean, I’m not into dudes, but if I were, he’d certainly be my type,” Charlie said.

“Yeah, he’s definitely my type. I’d ask him out if it weren’t my professor,” Anna added.

“I’m considering asking him out, even though he is our professor,” Meg said.

“With everyone talking about how attractive they find Dr. Novak, I’m starting to think that’s the reason Dean goes to Dr. Novak’s office hours so often. He’s going to stare at him and flirt with him,” Charlie joked.

“Yeah right,” Dean laughed awkwardly, “Anyway, we should be getting back to studying, right?” 

“Nah, looks like Dean actually goes there for studying, since he seems to care so much about that,” Meg said.

They studied for a couple more hours and were able to cover everything that would be on the midterm. Every time someone had a question, Dean was able to answer it and go in depth about it. Of course, Anna constantly was flirting with him. Laughing a little too much anytime Dean cracked one of his cheesy jokes, when everyone else just rolled their eyes. She was constantly in his personal space, rubbing her hands over Dean’s arms, constantly finding any excuse to touch him. She’d bat her eyelashes constantly. And every few minutes she’d say, “Wow, Dean, you’re so smart,” or something similar, once Dean answered someone’s question.

After they were finished with studying, they all collected packed up their stuff and got ready to leave.

“Y’know, Dean,” Anna started, “I can’t believe someone as smart and attractive as you isn’t dating anyone,”

“Well, you know, just busy right now,” Dean shrugged her off.

Dean was about to leave when Anna pulled him aside, “Hey, Dean. Why don’t we get together tomorrow night, just the two of us, and get some extra studying done,”

“Uh, I actually can’t tomorrow. I’m showing my brother around the city,” Dean lied.

“Oh, well, maybe another time then,”

“Yeah, maybe. Listen, I gotta go, it’s gonna be an early day for me, so I’ll see you later,” Dean said, leaving.

_Now, Saturday evening_

Dean had spent all day getting work done for his engineering classes, since he spent all of last night with his mythology study group. He was more than ready for a night out with his favorite professor. Dean took out his phone and let Cas know he was ready for their night.

To Cas: _Hey, I’m almost ready. Where are you?_

From Cas: _I’m parked a couple blocks away. Figured it wouldn’t look good for a professor to show up at a student apartment building_

To Cas: _Good point. I’ll be right down. What kind of car should I look for?_

From Cas: _Silver Toyota Camry_

To Cas: _Really, Cas. A Camry?_

From Cas: _Yes, Dean. They’re great cars. Reliable with great gas mileage. Not to mention very safe, unlike that old pile of metal you own_

To Cas: _DON’T YOU DARE TALK ABOUT BABY LIKE THAT_

From Cas: _My apologies, Dean_ Cas added the little eye-rolling emoji to the end of the text.

To Cas: _You’re lucky you’re cute_

Dean sent his last text before heading to meet Cas. As he was passing through the lobby, he ran into Anna.

“Hey, Dean,” Anna said.

“Oh, hey,”

“Going to meet your brother?”

_What’s she talking about? Oh, that’s right. I told her I was taking Sam out_

“Yeah, yeah. He’ll be here soon, so I gotta run, but have a good night,” Dean said, running out.

Dean quickly found Cas’ car and hopped in.

“Hey, Cas,” Dean gave Cas a long, desperate kiss on the lips. He was so glad to be with Cas tonight.

“Well someone’s missed me,” Cas said, a little breathless from Dean’s kiss.

“Yeah, things got a little weird last night, so I’m just glad to be spending the night with you,”

“What do you mean?” Cas asked, starting to drive off.

“Well, things were starting off well. We were studying, and I actually knew the answers to the questions people had,”

“See, I told you, you know more than you think,”

Dean blushed, “Yeah, well, we took a study break, and things went downhill from there. One of the girls in the group kept hitting on me and flirting with me and even asked if I wanted to have an extra study session with just the two of us tonight. I told her I was taking my brother out tonight and showing him around,”

“Sorry about that, Dean,” Cas said, “Or, did you enjoy it?” Cas asked, timidly.

“No, Cas. I mean, I won’t lie and say it doesn’t make me feel good when someone finds me attractive. It’s nice. But you have nothing to worry about it. I’m not interested in her. It was annoying, actually. Nothing happened, Cas. I promise,”

“Good. I trust you, Dean. I know it’s only been a little over a month, but I know I can trust you,”

“You can, Cas,” Dean said, before adding, “Oh, and all the girls were talking about how cute you were,”

“Really?” Cas tried to hide his amusement. 

“See, you’re not the only one who gets excited when someone finds them attractive,”

“Well, it’s a common human thing to get excited when someone finds something intriguing about you, whether it looks or talents or something else,”

“Yeah, I guess that’s true. So, where are we going tonight for dinner?” Dean asked, changing the subject.

“It’s still a surprise. It’s a wonderful restaurant,” Cas said, keeping his lips sealed.

“Not even a hint?”

“Nope,” Cas grinned.

“Fine. We’re at least doing our usual karaoke,”

“But we’re in my car and we don’t have your tapes,”

“True, but you do get the local classic rock station. We can listen to that,”

“I don’t what channel that is,”

“I do. Hang on,” Dean reaching over to change the station to the classic rock one.

For the rest of the ride, the two of them sang, practically yelling. When they parked, they realized they’d have to be quiet.

“I’m impressed, Cas. You knew the words to most of the songs,” Dean said, when he got out of the car.

“Well, I have been listening to some classic rock songs on YouTube after you introduced me to them,” Cas confessed, “I’m starting to like them,”

“I’m glad,” Dean smiled, “So, now that we’re here, will you tell me anything about this place?”

“It’s one of the finest steakhouses in the state. I remember, during one of the times you came in to my office, you said that steak was your favorite thing to eat, yet you’d never been to a really fancy steak place, so I figured I’d take you to one,”

“Wow, Cas. Thank you,” Dean was blown away.

“C’mon, Dean,” Cas opened the door for him.

“Hello, do you have a reservation?” the hostess greeted them.

“Yes, it’s under Novak for a party of two,” Cas replied.

“Ah, yes. Right this way,” the hostess said as she grabbed a couple menus and led them to their table.

“Your waiter will be right with you,” the hostess said and walked off.

“So, Dean, what do you think?”

“This place is so fancy,” Dean said, a little nervous.

“I’m guessing you’ve never been to a place like this before,” 

“Nope. We could never afford a place like this not mention my blue-collar family would look so out of place at a restaurant like this,”

“Well, I know what you mean. The people that come here are very upper-class and often more concerned with what brands their outfits are and how big their houses are than how good of people they are,” Cas said.

“You almost sound like you’re speaking from experience,”

“I am. That’s the kind of family I’m from, and we went to restaurants like this all the time, and believe me the people here are not the kind of people I enjoy being around. My father thought that taking us to fancy places, whether they’d be restaurants or even vacations, would make up for that fact that he wasn’t really a father to us. He figured if he just bought us fancy things, he wouldn’t have to care or show up for us,” Cas explained.

“I’m sorry, Cas,” Dean comforted Cas.

“Well, at least I’m closer to my siblings because of it. We spent a lot of time together when our dad was away a lot. He traveled nearly every month for his job,” Cas added.

“Yeah, me and Sam are really close, because of all we went through. I guess if there’s a silver lining to it all, it’s that Sam and I became a lot closer to each other, because of it,” Dean stated.

“And from what you’ve told me about your father, so far, your father might be worse than mine, which is saying something,” Cas chuckled.

“Well, he certainly wasn’t the dad I’d had in mind. He was drunk constantly and always yelling at me or Sam. He lost his job, for showing up drunk so much, and couldn’t take that as a hint that he needed help. No matter what I, Sam, or my Uncle Bobby did, he refused to get help. Uncle Bobby basically raised us. He came over as often as he could and worked extra hours to help send us money to pay bills and buy food. Dad is now starting to put his life back together and get help. He’s sober for six months now. I don’t know what made him realize he needed help, but I’m glad he’s starting to do something,” Dean also explained his childhood woes.

“Well, that’s good, Dean. I’m happy for you,” Cas smiled.

“Thanks. So, how about we order our food and talk about something else other than who had the worst dad growing up?” Dean suggested.

“I like that idea,” Cas said.

Cas got the waiter’s attention, so they could order their meals. 

“So, Cas, gonna tell me anything about the play we’re seeing tonight?” Dean asked.

“I wasn’t sure what to choose, but I figured after you confessed to me that you enjoy romantic comedies, I figured how about a classic play that has both romantic and comedic elements in it,” Cas started.

“Sounds good so far,” Dean replied.

“It’s a local theatre group’s production of _A Mid-Summer Night’s Dream_. I wasn’t sure if you were okay with Shakespeare, but it’s a modern take on it and I’ve heard wonderful things about it, from the few people I know who have seen it,”

“That was actually one of my favorite Shakespeare plays to read in English class in high school,”

“Really?” 

“Yeah, you wanna know another secret of mine?” Dean asked.

“Absolutely,”

“I actually like reading Shakespeare and took it as an elective last year,”

“I’m not surprised, actually. Now that I know you love romantic comedies and you love seeing action, it makes sense. Shakespeare has a lot of romance, comedy, action, and you have to be an intelligent person to read them. It seems like the perfect thing for you,”

“Thanks, Cas. Not many people often complement me on how smart I am,” Dean confessed.

“Then they clearly don’t pay enough attention to you,” Cas replied, sincerely.

“You know, after that talk with you on the phone, I felt more confident. It felt nice for someone to see something in me and help encourage me. You brought out something amazing in me. I guess that’s what makes you a good boyfriend and a good teacher,” Dean confessed.

Cas didn’t know how to respond to Dean’s confession, so he leaned in and gave Dean a long, slow kiss.

When their food arrived, Dean and Cas talked about some of their favorite things about the city and things they usually did on a Saturday night. When the dinner was over, Cas paid for them. He led Dean to the theatre where they were going to see the play. They took their seats in the theatre and waited for the play to start. As soon as the theatre darkened, Dean did something he’d been waiting to do since Cas told him they were going to see a play. Dean reached over and pretended to yawn and stretch as he put his arm around Cas. The most classic and cheesiest move a guy can pull. Dean shifted his gaze from the stage to Cas. When Cas felt Dean’s arm around him, he rolled his eyes at Dean. Dean winked back.

“It’s a good thing you’re cute,” Cas whispered in a sassy tone.

“I know I am,” Dean sassed back.

“Just shut up and watch the play,” 

“Yes, Dr. Novak,” Dean teased.

The two sat in silence, leaning towards each other as they watched the play. During intermission, they went out in the lobby to grab a drink. Dean was standing next to Cas making small talk with some people near them, when he noticed someone he knew.

“Oh, shit,” Dean suddenly said.

“What is it?” Cas asked concerned.

“That girl over there with the red hair in the blue dress is Anna,” Dean said, subtly pointing to his right.

“Shit. What are we gonna do?”

“I don’t know but she can’t see us together. What’s she gonna think?”

“Not to mention you told her you were supposed to be spending the evening showing your brother around,” Cas added.

“Let’s just hope she’s not sitting near us,”

“Dean, go hide in the men’s room. I’ll watch her to make sure she goes to her seat and the theatre’s dark before I tell you to come out again, so she won’t see us,”

“Okay. You know, this is kind of thrilling,” Dean confessed, “Sneaking around and hiding, because we’re not supposed to be dating,” Dean said excitedly.

“I hate to admit this, but you’re right. I’m enjoying the thrill of it, running around, trying not to be caught,”

“We really shouldn’t get this excited over something like this, but I’m having too much to care,” Dean ran off to go hide in the men’s room.

After Dean left, Cas sipped his drink and tried to look casual, while he kept glancing up, looking at Anna. As soon as Cas noticed Anna was gone, he quickly followed her to see where she was sitting and make sure that she stayed in her seat. Most people were making their way back into the theatre for the second half of the play, so the lobby was starting to empty. Cas scanned the theatre for Anna and saw she wasn’t sitting near them. Cas breathed a sigh of relief.

To Dean: _Anna’s back in her seat. She’s sitting far away from us. It’s safe to come back now_

From Dean: _Great. I’ll make my way back now_

Dean and Cas both sat back in their seats to watch the play. They got halfway through the second half of the play when they caught each other’s gaze. They leaned towards each other and their lips met. As their lips moved against each other’s, Dean moved from his chair to Cas’ lap, where he stayed for the rest of the play, Cas’ arms wrapped around Dean’s waist, Dean’s hands in Cas’ hair. The couple made out the entire time. When the play was over, Cas’ hair was a complete wreck and his tie was loosened. Dean didn’t look much better, his lips red and swollen and top two button of his dress shirt open. Both enjoyed the play, but enjoyed making out with each other more. Dean and Cas were thankful the lights were still dim when the cast came out for the final curtain call, so they could fix themselves before they left.

They waited until they saw Anna leave, before they left. After they exited the theatre, they went for their midnight walk around town, still smiling from their make out session. Cas suggested to go near the path near a pond that was lit by romantic street lights. Cas held Dean’s hand as he led him down the path. They talked the entire time. It was so easy. Dean felt so calm around Cas. Dean made Cas’ happy. They both felt they could completely be themselves around the other, like they didn’t have to hide any part of themselves, and felt they could share anything. Dean felt himself starting to fall in love with Cas. He’d know he’d always remember how beautiful Cas’ eyes looked. Dean was sure they were brighter than the moon. He was taken by how amazing Cas looked, his slightly messy black hair, blowing in the light breeze. Dean didn’t know it, but Cas felt the same way. The moonlight made Dean’s green eyes sparkle and brought out his freckles. It was only a matter of time before they confessed their love.

**Author's Note:**

> Okay, I really hope you like this chapter, because I really liked it. Let me know what you think!
> 
> Follow me on Twitter: Beaniejedi33


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